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Doesn't Hurt to Ask

Using the Power of Questions to Communicate, Connect, and Persuade

By Trey Gowdy
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Doesn't Hurt to Ask by Trey Gowdy

Doesn’t Hurt to Ask (2020) teaches the subtle art of persuasion through one unconventional tool: asking questions. Former congressman Trey Gowdy explains how thoughtful questions can help you reach your audience, communicate your message, and win people over – whether that’s in a courtroom, a business meeting, or at the dinner table.

Key idea 1 of 9

Persuasion is a subtle art, and questions are its greatest tools.

Are you ready to start winning every argument you ever have? Are you ready to grind your opponents into the ground with your debating skills?

Then these blinks are not for you.

Persuasion isn’t about annihilating your opponents. It’s about listening to them, communicating with them, and advocating for your own beliefs in a compelling way. Think about it: how many times have you changed your mind because someone kept bombarding you with their opinions?

Questions work so well because they put the focus on your conversation partner, and nudge them in the right direction without making them react defensively. The author knows about this firsthand. He only got into law after a friend’s mom asked him a bunch of really great questions.

The key message here is: Persuasion is a subtle art, and questions are its greatest tools.

The author had always planned to work construction jobs with a friend when he’d finished high school. One day though, his friend’s mom picked up on the topic. She asked him, “What are you going to do next, honey?” After he answered, she asked a follow-up question. And then another one. And another one. By the end of the interview, he had decided that he wanted to become a lawyer.

His friend’s mother didn’t make a single evaluative statement to persuade him – she simply let him persuade himself. That’s the power of asking questions.

Now, let’s make one thing clear before you get started: there is such a thing as a stupid question. One time during a robbery trial, the author’s witness reported that the suspect “had a blue bag in his hand.” The author immediately fired off a follow-up question: “Okay, what color was the blue bag?” The laughter that ensued in the courtroom should be proof enough that stupid questions do exist.

Still, any stupid question is better than a stupid assertion. Imagine someone asking you, “Who wrote Hamlet?” That question reveals a pretty big knowledge gap. But now imagine someone telling you, “George Washington wrote Hamlet.” That’s not just a knowledge gap; that’s a knowledge gap the person isn’t even aware of. Who would you trust more in an honest debate – a person who is uninformed, or a person who is misinformed?

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